Phenylboronic Acid → HCID 58091615, compound

HRID 1874009Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]2[O:8][C:9]3[N:26]=[C:25]([C:27]4[CH:37]=[CH:36][C:30]([C:31]([N:33]([CH3:35])[CH3:34])=[O:32])=[CH:29][CH:28]=4)[CH:24]=[CH:23][C:10]=3[CH:11]([C:12]([CH3:22])([CH3:21])[C:13](=[O:20])[NH:14][C:15]3[S:16][CH:17]=[N:18][N:19]=3)[C:5]2=[CH:4][CH:3]=1.[C:38]1(B(O)O)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[CH3:21][C:12]([CH:11]1[C:5]2[C:6](=[N:7][C:2]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[CH:3][CH:4]=2)[O:8][C:9]2[N:26]=[C:25]([C:27]3[CH:37]=[CH:36][C:30]([C:31]([N:33]([CH3:35])[CH3:34])=[O:32])=[CH:29][CH:28]=3)[CH:24]=[CH:23][C:10]1=2)([CH3:22])[C:13](=[O:20])[NH:14][C:15]1[S:16][CH:17]=[N:18][N:19]=1

Participants

Reactant 2

HCID 66827Phenylboronic Acid

HCID 58091600HCID 58091600, compound

Product 1

HCID 58091615HCID 58091615, compound

Procedure

Using a two-step sequence for the synthesis of Example 64, Example 65 was synthesized from the acid from Step 4 of Example 54 and phenylboronic acid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.90 (1H, s), 8.13 (2H, d, J=8.31 Hz), 8.08 (2H, d, J=6.80 Hz), 7.43-7.67 (9H, m), 4.64 (1H, s), 3.18 (3H, s), 3.05 (3H, s), 1.29 (3H, br. s), 1.28 (3H, br. s); MS (ES+) m/z: 577 (M+H); LC retention time: 3.96 min (analytical HPLC Method A).

Workup

customfor the synthesis of Example 64, Example 65

Sources & evidence

ORD record: ord-a826dccb3fcc4866a1d444342f65be7b
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304539B2

Reaction notes

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